Dress for Success: 4 Tips to Look (and Feel) Like a Confident Man

Published on: 17 November 2018 Last Updated on: 19 July 2019

You’ve always wanted to be the confident guy that commands the attention of everyone in the board meeting, and that gets numbers thrown at him in the local bar.

However, you’ve sometimes wondered if it’s your slovenly style, as opposed to your personality, that’s getting you passed over for dates and promotions.

In this post, we’ll tell you how you can dress like a confident man — even when you don’t actually feel like one.

Read on to learn how the right clothes can communicate an air of experience, control, and even approachability.

We bet that, once you follow these tips, you’ll walk with a little more swagger in your step.

1. Have Your Clothing Tailored:

A tailor can make even an affordable suit from the discount bin look like it was created especially for you.

Plus, especially with sizing as inconsistent as it is these days, taking your clothing to a tailor ensures that your sleeves are the right length, and that your slacks aren’t covering half of your feet.

Plus, well-fitting clothing means that you can show off the body you’ve been working so hard for in the gym!

We guarantee that you’ll feel like a totally confident man when you’re wearing clothing that works with your height and your body shape. Plus, taking one of your best-loved (put perhaps a little well-worn) suits or shirts to the tailor can give it a completely new and modern look.

Everyone will assume you were able to get a bespoke made especially for you.

2. Invest in the Right Accessories:

No, we don’t mean that you have to start piling on the man jewelry — though if that’s your thing, you should totally go for it.

Instead, getting the right accessories to turn you into a confident guy who can command the attention of any room is all about knowing how to make the right investments.

There are a few accessories that every man needs in his wardrobe.

First, invest in a leather briefcase or a messenger bag. This will make you feel like you have somewhere important to go (even if all you’re really doing is heading to your local grocery store.) We love the idea of a messenger bag that’s been stamped with your initials, to give it a more personalized touch.

You also need to ensure that you have a few essential shoes that all confident men have in their own closets.

If you don’t have a pair of Chelsea boots, some black and brown dress shoes, and one “wild card” shoe (like a fun pair of velvet slippers or some designer sneakers?)

Invest in some now.

Not only can a nice pair of shoes pull a whole outfit together. You’ll likely actually end up saving on shoes because you’re not buying a $100 pair that will fall apart after every season. Shop for the long game.

Finally, make sure you’ve explored all your options when it comes to watches for men. Whether you’re on the hunt for a bold, look-at-me statement watch, a dive watch, or even if you’d prefer to go digital?

The right watch can make you feel like the confident man you’ve always wanted to be.

3. Good Grooming is Key:

A confident man is also one that takes good grooming and skincare seriously.

Even the most expensive and fabulous designer suit can end up looking cheap if it’s worn with unwashed hair, an unkempt beard, and a unibrow.

Especially as more and more men feel comfortable getting more into grooming rituals, we encourage you to explore which ones you’re the most interested in trying out for yourself.

You don’t have to go out to the most cutting-edge salon in town and drop hundreds of dollars on the most fashionable haircut of the moment. Instead, it’s about regular maintenance of the classic cuts you love.

It’s also about making sure your nails look healthy, taking care of unwanted body hair, or just doing any kind of grooming ritual that makes you feel good.

Plus, many companies are making beauty products geared specifically towards men. This means you won’t have to raid your girlfriend’s bathroom cabinet anymore.

4. Don’t Let Trends Turn You into a Fashion Victim:

Dad sneakers, skinny ties, and street style may be the latest thing in men’s fashion.

But if you truly want to know how to be a confident man, you need to get real with yourself about whether or not an overly-trendy outfit is making you look like a try-hard.

If a “trend” isn’t something that you’d normally wear in real life? Perhaps it’s better left on the runways as opposed to in your closet.

Instead, focus on timeless pieces. Instead of spending $400 on a fanny pack (yes, it happens) put that money towards an elegant Italian leather wallet or a well-tailored white dress shirt.

If you love dressing en vogue, we suggest to wearing one trend at a time. After all, you don’t want to end up looking like a fashion magazine thew up on you.

Become a Confident Man with These Tips:

You’ve heard the saying, “Dress for the job you want, not the one you have.” The same can be said of “dressing like the man you want to become.”

Eventually, you won’t feel like you’re pretending to be a confident man anymore. You’ll realize that you’ve always been one all along, but that you just needed a few style updates to remind you of that.

So, what else can you do to upgrade your looks, your lifestyle, and your wardrobe?

No matter your job, your income level, or the kinds of things you like, we’ll help you to learn more about how to express yourself the right way.

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